With Baltimore in 1899, Sheckard led the league with 77 stolen bases. He played in four World Series with the Cubs, winning championships in 1907 and 1908; and he led the league in 1911 with 121 runs and 147 walks – a major league record until broken by Babe Ruth in 1920, and still a team record.

Sheckard was also the first man to lead the league in homers and steals in the same season (1903). Ty Cobb (1909) and Chuck Klein (1932) are the only other players to do so in the majors.

Sheckard was also an excellent outfielder. He holds the all time single season major league record for double plays at two separate positions. His 12 double plays as a left fielder in 1911 for the Cubs is 2 more than any other left fielder in history. And in 1899, while playing for the Baltimore Orioles, Sheckard played right field and set the record for double plays by a right fielder with 14. See related article on All Time Double play leaders.